J Incl Phenom Macrocycl Chem
Fig. 12 Changes in the UV–Vis spectra of 4 in DMSO after addition of F- (6.5 equiv) with increasing amount of a 1.5 equiv of Cu2? and b 1.7
equiv of Ni2?
respectively. H and 13C NMR spectra were recorded in
DMSO-d6 on a 300 MHz Bruker DPX 300 instrument
using tetramethylsilane (TMS) at 0.00 as an internal stan-
dard. Mass spectrum was recorded on a Bruker Compass
Data Analysis 4.0 Mass spectrometer. A Perkin Elmer
Lambda 35 double beam spectrophotometer with variable
bandwidth was used for the acquisition of the UV–Vis
molecular absorbance. Melting points were determined on
an electrothermal melting point apparatus obtained from
M/S Toshniwal and were uncorrected.
1.30 (t, 6H), 1.07(s, 18H); 13C NMR (75 MHz, DMSO-d6,
d in ppm) 14.43, 18.98, 31.46, 34.37, 56.50, 61.36, 72.48,
116.17, 116.68, 121.01, 122.63, 125.36, 126.40, 128.49,
129.22, 131.37, 132.48, 139.72, 145.09, 146.96, 147.53,
150.87, 151.05, 155.55, 161.64, 161.97, 169.36.
1
Analytical data for reference compound 7
Light green solid; Yield: 73 %; Mp: 271 °C; UV (kmax
,
DMSO): 317 nm; HRMS (ESI–MS) m/z:calcd 308.1030,
found 308.1017; IR (KBr pellet, cm-1): 3,350.68,
2,925.0835, 1,579.01, 1,101.72; 1H NMR (300 MHz,
DMSO-d6, d in ppm): 11.98 (s, 1H, NH, D2O exchange-
able),11.95 (s, 1H, NH, D2O exchangeable), 10.03 (s, 1H,
OH, D2O exchangeable), 8.20 (s, 1H), 7.75 (d, 1H), 7.57
(d, 2H), 7.38 (dd, 1H), 7.22 (dd, 1H), 7.15 (d, 1H), 6.83 (d,
2H), 6.67 (s, 1H); 13C NMR (75 MHz, DMSO-d6, d in
ppm) 116.23, 116.64, 119.9, 120.99, 122.66, 125.33, 125.9,
129.59, 131.44, 139.73, 145.07, 149.71, 160.2, 161.61,
162.01.
General procedure for the synthesis of receptor 4
and reference compound 7
5,17-diformyl-11,23-bis(p-tert-butyl)-26,28-bis(ethoxycar-
bonyl methoxy)-25,27-dihydroxy calix[4]arene was
refluxed with 2-oxo-1,2-dihydroquinoline-4-carbohy-
drazide (2 mol equivalent) in dry ethanol for 12 h. The solid
product thus separated out was filtered and recrystallised
from ethanol to yield pure product 4 as a light green solid.
2-Oxo-1,2-dihydroquinoline-4-carbohydrazide(1 equiv)
was refluxed for 8 h with p-hydroxybenzaldehyde in ethanol.
Solid thus obtained was fitered and recrystallised from eth-
anol to afford the reference compound 7 in its pure form.
Acknowledgement Tanu Gupta thanks the CSIR, India for research
fellowship. Financial assistance from DST (FIST grant for HRMS to
Department of Chemistry, IIT Delhi) and MoRD is gratefully
acknowledged.
Analytical data for 4
References
Light green solid; Yield: 75 %; Mp: 288 °C; UV (kmax
,
DMSO): 327 nm; HRMS (ESI–MS) m/z:calcd 1,135.4811,
found 1,135.4810; IR (KBr pellet, cm-1): 3,384.61,
2,956.04, 1,728.40, 1,610.44, 1,196.19; 1H NMR
(300 MHz, DMSO-d6, d in ppm): 12.004 (s, 2H, NH, D2O
exchangeable), 11.891 (s, 2H, NH, D2O exchangeable),
8.418 (s, 2H, OH, D2O exchangeable), 8.352 (s, 2H), 7.786
(d, 2H), 7.578 (m, 6H), 7.39 (d, 2H), 7.22 (dd, 2H), 7.0 (s,
4H), 6.715 (s, 2H), 4.78 (s, 4H), 4.31 (m, 8H), 3.59 (d, 4H),
1. Maity, D., Govindaraju, T.: A differentially selective sensor with
fluorescence turn-on response to Zn2? and dual-mode ratio-
metric response to Al3? in aqueous media. Chem. Commun. 48,
1039–1041 (2012)
´
2. Alfanso, M., Tarraga, A., Molina, P.: Ferrocenyl benzobisimi-
dazoles for recognition of anions and cations. Inorg. Chem. 52,
7487–7496 (2013)
3. Kim, S.K., Lynch, V.M., Young, N.J., Hay, B.P., Lee, C.H., Kim,
J.S., Moyer, B.A., Sessler, J.L.: KF and CsF recognition and
123